Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
  • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
  • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals

Definitions

• This invention relates to herbicidal compositions, preparation thereof and processes of controlling unwanted plants using the herbicidal compositions.
• the SF-1293 substance (in the free acid form) is the compound of the formula: ##STR1##
• the SF-1293 substance is highly active to various fungal diseases of plants, including Pellicularia sasakii (sheath blight on rice) and Piricularia oryzae (rice blast).
• the SF-1293 substance exhibits a considerably high herbicidal effect when applied at a rate of about ten times higher than that at which it has been used as fungicide.
• the SF-1293 substance, and various salts thereof are herbicidally active to growing annual and perennial weeds as well as various bushes and trees, and that upon foliage treatment, they can severely damage or kill the overground segments of the plants and strongly inhibit regrowth of the plants from their underground rhizomes.
• a process of severely damaging or killing unwanted plants which comprises applying to the plants or to the growth medium thereof, a herbicidally effective amount of the SF-1293 substance as defined in hereinafter or a salt thereof.
• SF-1293 substances The SF-1293 substance (the free acid form) and salts thereof (hereinafter collectively referred to merely as “SF-1293 substances") are effective to severely damage or kill unwanted plants both when applied directly to the plants ("post-emergence application”) and when applied to soil or other growth medium where the plants are growing, to prevent the emergence of seedlings of the plants ("pre-emergence application").
• the SF-1293 substances for use in this invention are advantageous in that they may be applied at an optional time in all seasons and that they are effective not only as a contact herbicide but also as a translocated or systemic herbicide. Further, they have favorably the unique feature that they are non-phytotoxic to useful woody plant, Chamaecyparis obtusa (Japan cypress, "hinoki” in Japanese, which provides a wood material extensively used in the construction of furnitures and houses) but they are highly toxic to unwanted bushes and weeds growing in the area where the useful woody plants occur naturally or are cultivated artificially.
• this invention provides a process of selectively controlling the growth of weeds and bushes in the area of Chamaecyparis obtusa, which comprises applying to the area the SF-1293 substance or a salt thereof in an amount sufficient to inhibit the growth of the weeds and bushes.
• N-phosphonomethylglycin which is usually known as glyphosate
• the antibiotic SF-1293 substance which acts similarly to glyphosate, is very superior to glyphosate in respect of the herbicidal properties and weed-control spectrum.
• the SF-1293 substance is effective at a lower concentration, more rapidly develops the herbicidal effect and shows a much wider spectrum of weed control, and further it is absolutely non-phytotoxic towards Chamaecyparis obtusa as already stated.
• glyphosate disadvantageously shows a phytotoxicity to Chamaecyparis obtusa.
• glyphosate is much less active to broadleaved weeds and perennial weeds such as Rumex japonicus and Cayratia japonica.
• the SF-1293 substance is equivalently active against the weeds irrespective of weed species at the same application rate and completely suppresses regrowth or recovery of perennial weeds.
• non-crop land, orchard, forestry land and grassland can be infested with annual and perennial weeds and various bushes.
• either treatment of applying a mixture of two or more herbicides at once or treatment of applying different or same herbicide(s) several times at intervals may be employed. Both of these herbicidal procedures, however, are very complicated and disadvantageous in the cost and labor involved therein.
• the SF-1293 substances are highly active against almost all weeds, bushes and trees except for Chamaecyparis obtusa, so that application of the SF-1293 substances alone can controll all of the undesired plants, inclusive of weeds and unwanted trees, as intended.
• the SF-1293 substances can prevent regrowth or recovery of the undesired plants, indicating that they are a herbicide of particular great value in practice.
• the SF-1293 substances are effectively applied for land preparation in forestry land, control of bottom weeds growing in forestry land of Chamaecyparis obtusa, control of weeds and bushes in grassland, bottom weed-control in orchard and inhibition of weed growth in non-crop land, and further they are suitable for pre-sowing treatment in uncultivated upland, by utilizing their properties that they will become inactivated at a relatively high rate in soil.
• the SF-1293 substances are also suitable for "spot" herbicidal treatment in crop area or lawn area infested with vicious perennial weeds.
• SF-1293 substances used in the process of the invention are usually applied in the form of a composition comprising the SF-1293 substances as the active ingredient which is mixed with a liquid or solid diluent or carrier.
• this invention provides a herbicidal composition comprising as active ingredient at least one member selected from SF-1293 substance of the structural formula: ##STR2## and salts thereof, in admixture with a diluent or carrier.
• composition of the invention may generally comprise the active ingredient in an amount of 0.01% to 50% by weight of the composition.
• this composition When applied to the heribicidal treatment, this composition usually may be diluted with water to a concentration of 0.05% to 5% with regard to the active ingredient.
• the salts of the SF-1293 substance which may be used as the active ingredient according to this invention include an alkali metal salt, an alkaline earth metal salt, a divalent-metal salt, an unsubstituted or substituted ammonium salt or an acid-addition salt which may generally be represented by the following formula: ##STR3## wherein M 1 and M 2 , which may be the same or different, each represents hydrogen atom or a cation selected from sodium, potassium, lithium, copper, magnesium, calcium, zinc, nickel and manganese, or an ammonium cation either unsubstituted or substituted by one, two, three or four lower alkyl, hydroxy-lower alkyl, particularly hydroxyethyl or lower alkenyl group; A represents an inorganic or organic acid selected from hydrochloric, sulfuric, hydrobomic, phosphoric, perchloric, nitric, acetic, propionic, citric, tartaric, monochloroacetic, trichloro
• composition of this invention may be in the form of aqueous solution, wettable powder, dusting powder, emulsion, granules or grains comprising the active ingredient in admixture with a suitable diluent or carrier.
• the solid compositions may be in the form of dusting powders or granules.
• Suitable solid diluents include kaolin, clay, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth, gypsum, Hewitt's earth, diatomaceous earth and vermiculite.
• Solid compositions may also be in the form of dispersible powders or grains comprising a wetting agent to facilitate the dispersion in liquids of the powder or grains which may contain also fillers and suspending agents.
• Liquid compositions include aqueous solutions, dispersions or emulsions which may be prepared by dissolving the active ingredient(s) in an organic solvent optionally containing wetting, dispersing or emulsifying agent(s) and then adding the mixture to water which may also contain wetting, dispersing or emulsifying agent(s).
• Suitable solvents are acetone, isopropyl alcohol, propylene glycol, diacetone alcohol, benzene, toluene, kerosene, methylnaphthalene and cyclohexanone.
• additives for example, additives for improving the distribution, adhesive power and resistance to rain on treated surfaces, the different compositions can be better adapted for intended purposes.
• compositions of the invention can comprise also other herbicides or plant-growth regulators known per se, for example, germination inhibitors so as to envisage enhancement of the herbicidal effect of the SF-1293 substances and extension of a period during which the substances remain active.
• compositions of the invention may also be in the form of liquid preparations for use as sprays which are generally aqueous dispersions or emulsions containing the active ingredient in the presence of one or more wetting agent(s), dispersing agent(s), emulsifying agent(s) or suspending agent(s).
• wetting agent(s) can be cationic, anionic, non-ionic or ampholytic agents.
• Suitable cationic agents are quaternary ammonium compounds, for example, cetyltrimethylammonium bromide and alkylpyridinium chloride.
• Suitable anionic agents are soaps, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), and salts of sulphonated aromatic compounds (for example, sodium dodecylbenzenesulphonate, sodium, calcium or ammonium lignosulphonate, butylnaphthalene sulphonate, and a mixture of sodium diisopropyl- and triisopropylnaphthalene sulphonates).
• Suitable non-ionic agents are the condensation products of ethylene oxide with fatty alcohols such as oleyl alcohol or cetyl alcohol, or with alkyl phenols such as octylphenol, nonylphenol and octylcresol.
• Other non-ionic agents are the partial esters derived from long chain fatty acids and hexitol anhydrides, the condensation products of the said partial esters with ethylene oxide, and the lecithins.
• Suitable ampholytic agents are alkyldimethyl betaine and dodecylaminoethyl glycine.
• Suitable suspending agents are hydrophilic colloids (for example, polyvinylpyrrolidone and sodium carboxymethylcellulose), and the vegetable gums (for example, gum acacia and gum tragacanth).
• compositions for use as aqueous dispersions or emulsions are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being diluted with water before use. These concentrates often should be able to withstand storage for prolonged periods and after such storage be capable of dilution with water in order to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment.
• the SF-1293 substance to be used as the active ingredient can be produced, as described in the specifications of U.S. Pat. No. 3,832,394 and German Pat. No. 2,236,599, by a microbiological process comprising cultivating a SF-1293 substance-producing strain of Streptomyces hygroscopicus under aerobic conditions to produce and accumulate the SF-1293 substance in the culture broth and recoving the active substance from the culture broth.
• the salts of the SF-1293 substance may be prepared by any convenient salt-forming method.
• the rate of application of the SF-1293 substances required to control unwanted plants will depend upon the identity of the plant species and the particular active compound selected for use as well as the climate conditions. However, in general, an application rate of 25 g. to 3000 g. per 10 ares is used. Our experiments have shown that it is most efficient for the herbicidal purpose to apply at a rate of about 100 l per 10 ares the liquid composition containing 0.01% to 0.05% by weight of the active ingredient to weeds of less than 10 cm in height or the liquid composition containing 0.05% to 0.2% by weight of the active ingredient to weeds of 10 to 30 cm in height.
• the SF-1293 substances are effective not only as the contact herbicide but as the translocated or systemic herbicide, thereby achieving the regrowth-inhibitory effect which is most important for control of perennial weeds and bushes.
• a herbicidal composition comprising as active ingredient a mixture of:
• the phenoxy herbicides include, for example, 2,4-dichlorophenoxyacetic acid (hereinafter referred to as 2,4-D) and salts, allyl ester and ethyl ester thereof, 2-methyl-4-chlorophenoxyacetic acid (hereinafter referred to as MCP) and salts, allyl ester and ethyl ester thereof, ⁇ -(3,4-dichlorophenoxy) propionic acid (hereinafter referred to as 3,4-DP) and its salts, d,l-2-(2-methyl-4-chlorophenoxy) propionic acid (hereinafter denoted as MCPP) and its salt, ⁇ -(2-methyl-4-chlorophenoxy) acetic acid (hereinafter denoted as MCPB) and its salt, d,l-2-(2,4,5-trichlorophenoxy) propionic acid (hereinafter denoted as 2,4,5-T) and its salts, and ⁇ -[4-(3,5
• the benzoic herbicides include, for example, 2,3,6-trichlorobenzoic acid (hereinafter referred to as TBA) and its salts, 3,6-dichloro-2-methoxybenzoic acid (hereinafter referred to as Banvel-D) and its salts and 3-amino-2,5-dichlorobenzoic acid (hereinafter referred to as Amiben) and its salts.
• TBA 2,3,6-trichlorobenzoic acid
• Banvel-D 3,6-dichloro-2-methoxybenzoic acid
• Amiben 3-amino-2,5-dichlorobenzoic acid
• the cholines include choline itself and choline salts, examples of which are salts of choline with an inorganic acid such as hydrochloric acid, phosphoric acid and carbonic acid or an organic acid such as acetic acid, oxalic acid and ascorbic acid.
• an inorganic acid such as hydrochloric acid, phosphoric acid and carbonic acid
• an organic acid such as acetic acid, oxalic acid and ascorbic acid.
• the diethylamines include diethylamine itself and its salts, examples of which are the salt with an inorganic or organic acid same as mentioned above for the choline salts.
• the salts of the SF-1293 substances which may be used in combination with the component (B) typically include those of the general formula (I) as defined hereinbefore.
• the herbicidal activity of the SF-1293 substances may be significantly enhanced when they are applied in combination with a wide variety of herbicides or synergists.
• a combination with a translocated herbicide or relatively slow-acting herbicide leads to maximum improvement in the herbicidal effect of the SF-1293 substances.
• the combined use of the SF-1293 substances and a biologically active substance with auxin activity can lead to salient improvement in the contact and systemic, herbicidal activities of the SF-1293 substances towards both broad-leaved perennial weeds and graminaceous perennial weeds and bring about extremely improved effect of inhibiting the regrowth of the weeds.
• Example 9 the combined use of the SF-1293 substances at 0.05% concentration and CMH at 0.3% concentration resulted in enhancement of both the contact herbicidal effect (when evaluation is made 21 days after the herbicidal treatment) and the regrowth-inhibitory effect (when evaluation is made 4 months after the herbicidal treatment), as compared to the case when the SF-1293 substances is used alone at 0.1% concentration.
• the use of the SF-1293 substance and CMH in combination allows the effect of the SF-1293 substances to be improved by twice and even by four to five times.
• the SF-1293 substances exhibit a wider spectrum of weed control when they are applied in combination with the compounds (B), as shown in Examples 11-15.
• the SF-1293 substances In order to ensure that the SF-1293 substances can achieve to the utmost the effect of inhibiting the regrowth of perennial weeds, it is necessary that they should translocate and migrate into the underground segments of the weed plant after foliage treatment but before killing of the foliage occurs.
• CMH may suppress regrowth of perennial weeds when it is applied in autumn season (see Japanese Patent Preliminary Publication No. 55835/76).
• CMH has the drawback that it can be normally applied only in autumn season, and that the overground segments of perennial weeds must be removed out by moving when CMH is applied in spring or summer season for the herbicidal purpose.
• CMH when CMH is applied in admixture with the SF-1293 substances, the latter gradually kill the overground segments while both CMH and the SF-1293 substances translocate into and kill the underground segments of the perennial weeds by the synergistic effect, resulting in complete suppression of regrowth of these weeds.
• the SF-1293 substances have no phytotoxicity to a useful tree, Chamaecyparis obtusa which dominates 25% of the area of the forestry land in Japan, and CMH is also non-toxic to the same. Accordingly, application of a formulation comprising a mixture of the SF-1293 substances and CMH to the area of Chamaecyparis obtusa (Japan cypress) resulted in efficient control of unwanted plants, particularly perennial weeds and bushes which are concurrently growing in said area. Besides, CMH, DPX-1108, cholines and diethylamines are likewise non-toxic to the cypress plant.
• compositions comprising a mixture of the SF-1293 substances and the compounds (B) can be applied for various herbicidal purposes in many areas and lands including crop area, forestry land, grassland, orchard and non-crop land, as previously described for the compositions comprising the SF-1293 substances alone as active ingredient. Further, the compositions may be applied in aquatic areas to control aquatic weeds and algae as well as in aquatic rice plant field after the harvest of the ripened rice plants.
• the ratio of the SF-1293 substances (A) to the compounds (B) to be incorporated in the compositions may vary over a wide range depending upon the nature of the compounds (B) and the envisaged use of the compositions. By way of general guidance, however, this mixing ratio may be in the range from 1:0.2 to 1:20 by weight. Usually, the weight ratio of the SF-1293 substances to each of the compounds (B) may be as shown in Table 1 below.
• the total amount of the SF-1293 substance (A) and the compounds (B) in the herbicidal compositions of this invention may generally be in a range of 0.05% to 80% by weight of the whole compositions.
• the composition may usually be diluted to an active ingredient concentration of 0.05% to 5% by weight.
• the amount of the SF-1293 substance applied usually may then be in a range of 25 g to 1500 g per 10 ares.
• compositions comprising the respective active compounds at concentrations indicated in Table 1 may be applied generally at a rate of 25 to 250 l, preferably 50 to 150 l per 10 ares.
• the amount of the SF-1293 substances to be used to kill perennial weeds and bushes and to inhibit regrowth thereof will be affected also by the surrounding climatic conditions, for example, temperature and intensity of light.
• the purposes envisaged can be attained by applying the SF-1293 substances at a rate of: 25 to 600 g per 10 ares for perennial weeds of 1 m or less in height (e.g. Artemisia princeps, Rumex japonicus, Cyperus rotundus etc.); 75 to 750 g/10 ares for perennial weeds of 1 m or more in height (e.g. Sasa nipponica, Miscanthus sinensis etc.) and small bushes (e.g.
• Rhododendron haempferi, Rubus crataegifolins etc. ares for big bushes (e.g. Castanea crenata, Quercus serrata etc.) as well as for control of fresh sprouts from big stumps.
• compositions comprising the mixed active compounds (A) and (B) can be formulated into any conventional form, including aqueous solution, dusting powder, wettable powder, emulsion, granule and grain using any known solid or liquid diluent or carrier by any convenient method, as detailed hereinbefore.
• Examples 1-3 illustrate the preparation of the compositions according to the invention.
• compositions in the form of dusting powder were prepared by mixing and grinding uniformly all the ingredients listed in above (3a) and (3b), respectively, in the proportions stated.
• the dusting powder may be directly applied for foliage treatment at a rate of 0.4 to 6 kg per 10 ares.
• Examples 4-8 illustrate the herbicidal properties of the SF-1293 substances.
• Upland soil was placed in a pot of 10 cm diameter and seeds of Digitaria adscendens (Crabgrass) were sown in the soil at a depth of 1 cm. After gently pressing the soil surface, the soil was sprayed evenly with solutions of SF-1293 substance sodium salt dissolved at different concentrations in 5 cc of water. 10 Days after spraying, the number of the seedlings of crabgrass was counted and percentage (%) of prevention of emergence was evaluated by comparison with untreated plots. For comparison, the tests were also conducted using glyphosate instead of the SF-1293 sodium salt. The results are shown in Table 2 below.
• Upland soil was placed in a pot of 10 cm diameter and seeds of crabgrass were sown in the soil at a depth of 1 cm from the soil surface.
• 1.2 ml (equivalent to 100 l/10a) of aqueous solutions of the test compounds at different concentrations as indicated in Table 3 below were applied evenly for foliage treatment. 10 Days after treatment, damage to plants was visually assessed on a scale of 0 to 10 where 0 indicates no effect and 10 indicates complete kill.
• Aqueous solutions containing sodium salt of SF-1293 substance at different concentrations as indicated in Table 4 below and 0.1% of actylphenylpolyoxyethanol as surfactant were prepared and applied at a rate of 150 l per 10 ares directly to spontaneously occurring perennial weeds at growth stages indicated in Table 4. 7 Days and 14 days after foliage treatment, damage to the plants was vissually assessed on a scale of 0 to 5 where 0 signifies no effect and 5 signifies complete kill.
• SF-1293 means monosodium salt of SF-1293 substance.
• Ht Helianthus tuberosus
• Pr Pueraria lobata
• Aqueous solutions containing sodium salt of SF-1293 substance at different concentrations indicated in Table 5 below and 0.1% of octylphenylpolyoxyethanol as surfactant were applied at a rate of 150 l/10a to the area where various bushes were spontaneously growing.
• 0 signifies no effect and 5 signifies complete kill as described in Example 6.
• Vb Viburnum dilatatum
• Table 5 shows that SF-1293 substance also exhibits a high herbicidal activity against woody plants irrespective of plant species.
• Aqueous solutions containing sodium salt of SF-1293 substance at different concentrations indicated in Table 6 below and 0.1% of octylphenylpolyoxyethanol as surfactant were applied at a rate of 150 l/10a to woody plants of about 60-70 cm in height. 7 Days and 14 days after treatment, damage to test plants was visually assessed on the same scale (0 to 5) as stated in Example 7. The results are tabulated in Table 6.
• Ch Chamaecyparis obtusa
• Examples 9-15 illustrate the synergistic effects achieved by the combined use of the SF-1293 substances (A) and the active compounds (B) as well as the herbicidal effects of the SF-1293 substances used alone.
• Formulations in the form of aqueous solution were prepared comprising as active ingredient different salts of SF-1293 substance (0.05% or 0.1%) or CMH(0.3%) or mixtures thereof and 0.1% of octylphenylpolyoxyethanol as surfactant.
• the aqueous solutions were applied at a rate of 100 l per 10 ares to Rumex obtusifolius at certain growth stage which was transplanted into pots of 20 cm in diameter. 21 Days after foliage treatment, damage to the test plant was visually assessed on a scale of 0 to 5 where 0 is no effect and 5 is complete kill as described in Example 6.
• Aqueous solutions containing the SF-1293 substances (A) and the components (B), in admixture or separately, at different concentrations indicated in Table 8 below were applied at a rate of 100 l per 10 ares to Rumex obtusifolius (abbreviated as Ro) and one of graminaceous perennial weeds, Zoysia japonica (abbreviated as Zy) which had been transplanted into pots at certain growth stage and taken root firmly in the pots.
• Table 8 shows that when the SF-1293 substances (A) or the compounds (B) is applied alone separately to Rumex obtusifolius and Zoysia japonica, there is obtained substantial damage of foliage of these weeds but little suppression of regrowth of these weeds from their underground roots, and that the combined use of the two components (A) and (B) can achieve complete suppression of such regrowth.
• Aqueous solutions containing monosodium salt of SF-1293 substance and CMH, in admixture or separately, and 0.1% of octylphenylpolyoxyethanol as surfactant were applied at a rate of 150 l/10 ares to spontaneously occurring perennial weeds at certain growth stage. Evaluation was made by the same gradings as indicated in Example 10 both for damage to plants (assessed 21 days after treatment) and for suppression of regrowth (assessed 4 months later).
• Pr Pueraria lobata
• Ch Calystegia hederacea
• Table 9 clearly shows that the mixture of monosodium salt of SF-1293 substance and CMH leads to remarkable improvement in suppression of regrowth and exhibits a wider spectrum of weed control.
• Formulations in the form of aqueous solutions similar to those used in Example 11 were applied at a rate of 150 l per 10 ares to plants growing in the area of Chamaecyparis obtusa. 30 Days and 3 months after foliage treatment, damage to plants was visually assessed on a scale of 0 to 5 where 0 is no effect and 5 is complete kill as described in Example 6.
• Ch Chamaecyparis obtusa
• Table 10 demonstrates that the mixture of monosodium salt of the SF-1293 substance and CMH considerably enhances the regrowth-inhibitory effect of the sodium salt but is non-phytotoxic to useful woody plant, Chamaecyparis obtusa.
• Formulations in the form of aqueous solutions similar to those used in Example 11 were applied at a rate of 100 l per 10 ares to spontaneously occurring weeds, Echinochloa crusgalli (abbreviated as Ec) and Digitaria adscendens (abbreviated as Dg) at intermediate growth stage. 14 Days and one month after foliage treatment, damage to plants was assessed. Besides, one month after treatment, degree of suppression of regrowth was evaluated, by the same gradings as indicated in Example 11.
• Hd Hydrangea hirta
• Rh Rhododendron kaempferi
• Rt Rhus trichocarpa
• Example 14 In order to evaluate the herbicidal effect of the SF-1293 substances against evergreen bushes, aqueous solutions similar to those used in Example 14 were applied at a rate of 100 l per 10 ares to Ternstroemia gymnanthera, Ligustrum japonicum and Rhaphiolepis umbellata (abbreviated as Tr, Lg and Ru, respectively). 5 Months after foliage treatment, damage to plants was visually assessed by the same gradings as indicated in Example 14.
• Aqueous solutions comprising sodium salt of SF-1293 substance as active ingredient and 0.1% of octylphenylpolyoxyethanol as surfactant were applied at a rate of 100 l/10 ares to Cyperus serotinus grown in a Wagner porcelain pot of 1/5000 a in cross-section. The pot thus treated was allowed to stand outdoors for about 3 months. Then, the tubers was taken from the underground soil in the pot and transferred into a deep petri dish. The dish was placed in the greenhouse for emergence. 21 Days later, evaluation was made for prevention of emergence on a scale of 0 to 5 where 0 is no effect and 5 is complete prevention of emergence.

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• 1978
  • 1978-10-31 GB GB7842540A patent/GB2007976B/en not_active Expired
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